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Preparation of photocyclizable dianthracene derivatives of resorc[4]arenes which are potential photoswitches

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Abstract

Resorc[4]arenes have been difunctionalized on opposite sides of the macrocycle using two anthracene units, which undergo intramolecular dimerization on irradiation at 350 nm. Syntheses and time-dependent photochemical experiments are reported.

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Notes and references

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  8. 6: 1H NMR (500 MHz, CDCl3): δ [ppm] = 8.38 (4H, d, J= 8.2 Hz, ArH), 8.14 (2H, s, ArH), 7.91 (4H, d, J= 8.8 Hz, ArH), 7.37 (8H, m, ArH), 7.01 (2H, s, ArH), 6.57 (2H, s, ArH), 6.17 (2H, s, ArH), 4.78 (4H, s, ArCH2), 4.52 (4H, dd, J= 8.5 Hz, J= 6.0 Hz, ArCHAr), 4.38 (4H, t, J= 4.4 Hz, CH2O), 4.10 (4H, t, J= 4.1 Hz, CH2O), 3.93 (12H, s, ArOCH3), 3.43 (12H, s, ArOCH3), 1.72–1.98 (8H, m, CH2), 1.15–1.45 (72H, m, CH2), 0.85 (12H, t, J= 7.2 Hz, CH3). ESI–HRMS: m/z calc. for C114H156O12Na: 1740.14890 ([M + Na]+); found: 1740.15045

  9. 7: 1H NMR (500 MHz, CD2Cl2): δ [ppm] = 8.44 (2H, s, ArH), 8.33 (4H, d, J= 8.8 Hz, ArH), 7.98 (4H, d, J= 8.8 Hz, ArH), 7.51 (4H, dd, J= 8.2 Hz, J= 6.9 Hz, ArH), 7.46 (4H, dd, J= 8.2 Hz, J= 6.9 Hz, ArH), 6.76 (2H, s, ArH), 6.74 (2H, s, ArH), 6.30 (2H, s, ArH), 5.41 (4H, s, ArCH2), 4.59 (4H, s, ArCH2), 4.47 (4H, t, J= 7.5 Hz, ArCHAr), 3.58 (12H, s, ArOCH3), 3.57 (12H, s, ArOCH3), 1.82 (4H, m, CH2), 1.75 (4H, m, CH2), 1.17–1.36 (72H, m, CH2), 0.87 (12H, t, J= 6.9 Hz, CH3). ESI–HRMS: m/z calc. for C112H152O10Na: 1680.12849 ([M + Na]+); found: 1680.12904

  10. 8: 1H NMR (500 MHz, CD2Cl2): δ [ppm] = 7.50 (2H, s, ArH), 6.94 (4H, d, J= 6.9 Hz, ArH), 6.73–6.82 (12H, m, ArH), 6.62 (2H, s, ArH), 6.59 (2H, s, ArH), 4.71 (4H, t, J= 7.5 Hz, ArCHAr), 4.56 (4H, s, ArCH2), 4.37 (2H, s, CH), 4.03 (12H, s, ArOCH3), 3.69 (4H, s, OCH2), 3.49 (12H, s, ArOCH3), 2.01 (4H, m, CH2), 1.81 (4H, m, CH2), 1.17–1.46 (72H, m, CH2), 0.88 (12H, t, J= 6.9 Hz, CH3)

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  1. Organische Chemie I, Universität Bielefeld, Postfach 100131, 33501, Bielefeld, Germany

    Christian Schäfer & Jochen Mattay

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  1. Christian Schäfer
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  2. Jochen Mattay
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Correspondence to Jochen Mattay.

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Schäfer, C., Mattay, J. Preparation of photocyclizable dianthracene derivatives of resorc[4]arenes which are potential photoswitches. Photochem Photobiol Sci 3, 331–333 (2004). https://doi.org/10.1039/b400351a

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